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We reported the first example of the synthesis of five- to seven-membered cyclic amino alcohols via the tributyltin hydride-induced radical cyclization of oxime ethers. a) Naito, T.; Tajiri, K.; Harimoto, T.; Ninomiya, I.; Kiguchi, T. Tetrahedron Lett. 1994, 35, 2205. We reported the application of this procedure to the preparation of the hexahydroazepine-containing fragment. In this case, a trans-cis mixture of cyclized products was obtained in 58% yield.
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22
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53649089164
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note
-
6b (3R, 4R)-4 was readily obtained by saponification of (3R, 4R)-5.
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23
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0024004050
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53649109465
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-
note
-
6: 330.1102, Found: 330.1115.
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-
-
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30
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53649110823
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note
-
Yield in parentheses is based on the consumed starting material.
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